This application is related to a co-pending application in the names of Harry R. Hinney and Jamil Baghdadchi which is directed to and entitled Process For the Preparation of Amine Terminated Polybutadiene, as well as a co-pending application in the names of Harry R. Hinney and Jamil Baghdadchi entitled Alkane- or Arenesulfonate Terminated Polybutadiene Compositions and Preparation Thereof filed concurrently herewith, which applications disclose certain aspects of the present invention.
In the above co-pending application of Hinney and Baghdadchi, entitled Process for the Preparation of Amine Terminated Polybutadiene, which application is incorporated herein by reference, there is disclosed a two step process for the preparation of amine terminated poly butadiene compounds via a particular method for the preparation of an alkane or arenesulfonate ester of polyhydroxybutadiene (sulfonate terminated polybutadiene), employed in the present invention. The instant invention is directed to novel amine terminated polybutadiene compositions and to the method for the preparation of such compounds by reacting an alkane- or arenesulfonate ester with a primary amine or ammonia.
Diamino terminated compounds containing sulfur dispersed in the carbon-carbon chain are described in U.S. Pat. No. 3,388,107. U.S. Pat. No. 4,015,061 describes the preparation of N,N-bis (triakylsilyl) amino terminated polymers by treating a lithio-N,N-bis (trialkylsilyl) aryl amine with a diene monomer which are converted to a mono- or di-primary aryl amine-ended polymer. U.S. Pat. Nos. 4,070,344 and 4,151,222 describes the preparation of anionically polymerized monomers such as conjugated dienes which are end capped with polyisocyanates or polyisothiocyanates which are then reacted with amide containing compounds to give an imide type end group. The imide type terminated polymer is hydrolyzed to form an amine terminated polymer. U.S. Pat. No. 4,316,967 describes an amine terminated polymer connected to an epoxy polymer to form a copolymer.
The amine terminated polybutadienes of the present invention are easily produced in high yield with a minimum of any side product formation. The amine terminated polybutadienes can be reacted with isocyanates to give polyurea resins or with esters and epoxides to form polyamides and epoxy resins respectively. The amine terminated polybutadienes may also be reacted with various other polymer segments such as polyimides, polyureas, etc. to give block or graft copolymers.
Applicants are not aware of any truly pertinent prior art that is deemed to be anticipatory or suggestive of the novel amine terminated polybutadiene compounds of the instant invention or the preparation thereof by reacting an alkane- or arenesulfonate terminated polybutadiene with a primary amine or ammonia to produce a secondary or primary amine terminated polybutadiene respectively.
It is an object of this invention to provide a novel class of amine terminated polybutadiene compounds including a method for their preparation.
These and other objects and advantages of this invention will become apparent from the description of the invention which follows and from the claims.